The synthesis, structural characterization and in vitro anti-cancer activity of novel N-{6-(ferrocenyl) ethynyl-2-naphthoyl} amino acid and dipeptide ethyl esters

被引：9

作者：

Harry, Andy G. ^{[1
]}

Murphy, James ^{[2
]}

Butler, William E. ^{[1
,2
]}

Tiedt, Rachel ^{[2
]}

Mooney, Aine ^{[1
,2
]}

Manton, Jennifer C. ^{[1
]}

Pryce, Mary T. ^{[1
]}

O'Donovan, Norma ^{[2
]}

Walsh, Naomi ^{[2
]}

Crown, John ^{[3
]}

Rai, Dilip K. ^{[4
]}

Kenny, Peter T. M. ^{[1
,2
]}

机构：

[1] Dublin City Univ, Sch Chem Sci, Dublin 9, Ireland

[2] Dublin City Univ, Natl Inst Cellular Biotechnol, Dublin 9, Ireland

[3] St Vincents Univ Hosp, Dept Med Oncol, Dublin 4, Ireland

[4] Teagasc Food Res Ctr, Dept Food Biosci, Dublin 15, Ireland

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2013年 / 734卷

关键词：

Ferrocene; Bioorganometallic chemistry; Dipeptides; Cytotoxicity; Lung cancer; RAY CRYSTAL-STRUCTURE; CANCER CELL-LINES; ANTIPROLIFERATIVE ACTIVITY; BREAST; FERROCENE;

D O I：

10.1016/j.jorganchem.2012.11.041

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

N-{6-(Ferrocenyl) ethynyl-2-naphthoyl} amino acid and dipeptide ethyl esters 2-8 were prepared by coupling 6-(ferrocenyl) ethyny1-2-naphthoic acid 1 to the amino acid ethyl ester GABA(OEt) and the dipeptide ethyl esters GlyGly(OEt), GlyAla(OEt), SarGly(OEt), SarAla(0Et), ProGly(OEt) and ProAla(OEt) using the standard N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDC), 1-hydroxybenzotriazole (HOBt) protocol. All the compounds were fully characterized using a combination of H-1 NMR, C-13 NMR, DEPT-135 and H-1-C-13 COSY (HMQC) spectroscopy, electrospray ionization mass spectrometry (ESI-MS) and cyclic voltammetry (CV). Compounds, 2-8 showed micromolar activity in the H1299 NSCLC cell line, with IC50 values in the range of 3.2-7.2 mu M. (C) 2012 Elsevier B.V. All rights reserved.

引用

页码：86 / 92

页数：7

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